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Preparation method of dicarboxylic acid

A technology of dicarboxylic acid and monocarboxylic acid, applied in the preparation of carboxylate, carboxylate, preparation of organic compounds, etc., can solve the problems of slow hydration reaction rate, limited reaction rate, low solubility, etc., and achieve high Reactivity and selectivity, high conversion and selectivity, less corrosive effect of equipment

Active Publication Date: 2019-12-27
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the close solubility of upstream materials such as cyclohexene and cyclohexane in water, the content of cyclohexane impurities in the cyclohexene raw material must be reduced as much as possible to reduce the negative impact of the dissolution effect of cyclohexane impurities on the reaction rate; as a raw material The oxygen content of reclaimed water has an impact on the hydration reaction and must be reduced as much as possible; 2) The hydration reaction rate is slow
Due to the difference in polarity, the solubility of cyclohexene in water is very small; resulting in the limitation of the reaction concentration on the reaction rate; 3) low conversion rate per pass
The hydration reaction of cyclohexene is a thermodynamic equilibrium-limited reaction. It is reported that even if the residence time of cyclohexene raw material in the slurry reactor is prolonged, the conversion rate of cyclohexene can only reach about 12%.
4) The reaction operation and subsequent separation and cycle costs are relatively high
In this method, because the reaction raw materials used in the addition reaction step are solid-liquid two-phase, it can only be operated intermittently, the reaction efficiency is not high, and the final product and raw materials are not easily separated.

Method used

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  • Preparation method of dicarboxylic acid
  • Preparation method of dicarboxylic acid
  • Preparation method of dicarboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] 60ml of macroporous strongly acidic ion-exchange resin Amberlyst15 is packed into the middle part of the stainless steel tubular fixed-bed reactor, and the top and bottom of the catalyst are filled with quartz sand respectively. The temperature of the reactor was raised to 90° C., and the reaction pressure was 0.1 MPa. The reactant cyclohexene and acetic acid enter the reactor separately, and the molar ratio of acetic acid to cyclohexene is 4:1. The feed space velocity of cyclohexene is 1.0g.g -1. h -1 . The reaction was run continuously for 250 hours. After the reaction product was collected, the composition of the product was analyzed by gas chromatography. The conversion rate of cyclohexene was 85.5%, and the selectivity of cyclohexyl acetate was 98.1%.

[0070] The addition reaction product is rectified to obtain cyclohexyl acetate with a purity greater than 99.5%. The cyclohexyl acetate was further oxidized, and the specific reaction steps were as follows: 14...

Embodiment 2

[0072] 60ml of macroporous strongly acidic ion-exchange resin Amberlyst35 is packed into the middle part of the stainless steel tubular fixed-bed reactor, and the top and bottom of the catalyst are filled with quartz sand respectively. The temperature of the reactor was raised to 90° C., and the reaction pressure was 0.1 MPa. The reactant cyclohexene and acetic acid are respectively fed into the reactor, and the molar ratio of acetic acid to cyclohexene is 4:1. The feed space velocity of cyclohexene is 1.0g.g -1. h -1 . The reaction was run continuously for 250 hours. After the reaction product was collected, the composition of the product was analyzed by gas chromatography. The conversion rate of cyclohexene was 84.2%, and the selectivity of cyclohexyl acetate was 98.2%.

[0073] The addition reaction product is rectified to obtain cyclohexyl acetate with a purity greater than 99.5%. The cyclohexyl acetate was further oxidized, and the specific reaction steps were as fo...

Embodiment 3

[0075] 60ml of macroporous strongly acidic ion-exchange resin Amberlyst36 is packed into the middle part of the stainless steel tubular fixed-bed reactor, and the top and bottom of the catalyst are filled with quartz sand respectively. The temperature of the reactor was raised to 90° C., and the reaction pressure was 0.1 MPa. The reactant cyclohexene and acetic acid are respectively fed into the reactor, and the molar ratio of acetic acid to cyclohexene is 4:1. The feed space velocity of cyclohexene is 1.0g.g -1. h -1 . The reaction was run continuously for 250 hours. After the reaction product was collected, the composition of the product was analyzed by gas chromatography. The conversion rate of cyclohexene was 81.5%, and the selectivity of cyclohexyl acetate was 98.1%.

[0076] The addition reaction product is rectified to obtain cyclohexyl acetate with a purity greater than 99.5%. The cyclohexyl acetate was further oxidized, and the specific reaction steps were as fo...

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Abstract

The invention discloses a preparation method of dicarboxylic acid, which comprises the following steps: 1) carrying out an addition reaction on a raw material system containing cyclic olefin and monocarboxylic acid under the action of an addition catalyst to generate an intermediate product system containing carboxylic acid cyclic ester; and 2) carrying out ring-opening oxidation reaction on the intermediate product system under the action of an oxidation catalyst to generate a corresponding dicarboxylic acid product. The addition reaction in the dicarboxylic acid synthesis route provided by the invention is high in one-way conversion rate, and the corresponding carboxylic acid cyclic ester is good in selectivity; in the addition-oxidation synthesis route provided by the invention, the addition reaction rate and the oxidation reaction rate are relatively high, and the yield of the corresponding dicarboxylic acid product is high. The synthetic route based on addition-oxidation providedby the invention is suitable for continuous and stable large-scale production of corresponding dicarboxylic acid products.

Description

technical field [0001] The application relates to a preparation method of a dicarboxylic acid, which belongs to the field of new technology of chemical production and manufacture. Background technique [0002] Dicarboxylic acid is an important chemical precursor raw material in polymer chemical industry and organic synthesis. Adipic acid is a representative substance among dicarboxylic acids, and currently, it is mainly produced by oxidation of cyclohexanol / cyclohexanone. Representative routes are: 1) oxidation of cyclohexane to cyclohexanol-cyclohexanone (KA oil), oxidation of KA oil to produce adipic acid; 2) hydration of cyclohexene to cyclohexanol, oxidation of cyclohexanol to hexyl Diacid. In the first production route, the one-pass conversion rate of cyclohexane in the step of oxidizing cyclohexane to KA oil is low (usually the conversion rate of cyclohexane is lower than 6%), the operating conditions of the reaction process are not easy to control, and accidents are...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C55/14C07C55/12C07C55/16C07C55/02C07C51/27C07C69/14C07C69/06C07C69/54C07C69/63C07C67/04
CPCC07C51/27C07C67/04C07C2601/08C07C2601/14C07C2601/18C07C69/14C07C69/06C07C69/54C07C69/63C07C55/14C07C55/12C07C55/16C07C55/02C07C51/31C07C51/316B01J23/8472B01J31/08C07C55/32B01J21/08B01J23/22B01J27/125B01J27/188B01J27/19B01J27/25B01J29/084B01J29/40C07C67/347
Inventor 黄声骏张大治
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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